(E)-2-(4-(4-methoxy-2,3-dimethylphenyl)but-2-en-2-yl)-1,3-dithiane | 1585153-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-(4-(4-methoxy-2,3-dimethylphenyl)but-2-en-2-yl)-1,3-dithiane
• 英文别名: 2-[(E)-4-(4-methoxy-2,3-dimethylphenyl)but-2-en-2-yl]-1,3-dithiane
• CAS: 1585153-90-7
• 化学式: C₁₇H₂₄OS₂
• 分子量: 308.509
• InChiKey: WRUWFZNHMDDETJ-WUXMJOGZSA-N

物化性质

• 熔点：
  61 °C
• 沸点：
  445.8±45.0 °C(predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-(4-methoxy-2,3-dimethylphenyl)but-2-en-2-yl)-1,3-dithiane 在 正丁基锂 、 碘 、 calcium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 5.0h， 生成 (2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)-Walsucochin B

  摘要：

  The first enantioselective total synthesis of the structurally unique nortriterpenoid (-)-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth-Gilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.

  DOI：

  10.1021/ol500553x
• 作为产物：
  描述：

  2-(4-甲氧基-2,3-二甲基苯基)乙醇 在 三氟化硼乙醚 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (E)-2-(4-(4-methoxy-2,3-dimethylphenyl)but-2-en-2-yl)-1,3-dithiane
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)-Walsucochin B

  摘要：

  The first enantioselective total synthesis of the structurally unique nortriterpenoid (-)-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth-Gilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.

  DOI：

  10.1021/ol500553x

文献信息

• Enantioselective Total Synthesis of (−)-Walsucochin B
  作者：Shiyan Xu、Jixiang Gu、Huilin Li、Donghui Ma、Xingang Xie、Xuegong She

  DOI：10.1021/ol500553x

  日期：2014.4.4

  The first enantioselective total synthesis of the structurally unique nortriterpenoid (-)-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth-Gilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.